Ammonia → 6-Amino-5-(2-ethyl-6-methylbenzyloxy)nicotinamide

HRID 427522Notes

Reaction equation

[CH2:1]([C:3]1[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[C:4]=1[CH2:5][O:6][C:7]1[C:8]([N+:26]([O-])=O)=[N:9][CH:10]=[C:11]([CH:25]=1)[C:12](OCC1C(C)=CC=CC=1CC)=[O:13])[CH3:2].[NH3:34]>CO>[NH2:26][C:8]1[C:7]([O:6][CH2:5][C:4]2[C:29]([CH3:33])=[CH:30][CH:31]=[CH:32][C:3]=2[CH2:1][CH3:2])=[CH:25][C:11]([C:12]([NH2:34])=[O:13])=[CH:10][N:9]=1

Participants

Conditions

Temperature: 35 °C

Procedure

2-ethyl-6-methylbenzyl 5-(2-ethyl-6-methylbenzyloxy)-6-nitronicotinate (0.7 g, 2 mmol) was added to a solution of ammonia in methanol (5-10%)(40 ml) and the mixture was stirred at 35° C. for 96 h. The solvent was evaporated under reduced pressure. Purification of the residue twice by column chromatography on silica gel using ethylacetate:methylene chloride (1:1) and methanol:methylene chloride (1:9) as eluent gave 0.14 g (31%) of the title compound.

Workup

customThe solvent was evaporated under reduced pressure
customPurification of the residue twice by column chromatography on silica gel

Sources & evidence

ORD record: ord-d58ea450e4c4469e9ba5fff702145922
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313137B1

Reaction notes

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